Why does auto weight paint do a poor job?
Thank you to @moonboots for the fix. My normals were flipped which was causing the weight paint algorithm to act funny. It was a quick fix to fix all the normals. All I had to do was select the normals that were facing the wrong direction and recalculate them using &quot;shift + N&quot;. After fixing the normals I reparented the armature and it did a much better job of assigning weights.